| Identification | More | [Name]
Meclizine dihydrochloride | [CAS]
1104-22-9 | [Synonyms]
1-([4-CHLOROPHENYL]PHENYLMETHYL)-4-([3-METHYLPHENYL]-METHYL)PIPERAZINE DIHYDROCHLORIDE
MECLIZINE DIHYDROCHLORIDE
1-((4-chlorophenyl)phenylmethyl)-4-((3-methylphenyl)methyl)-piperazindih
1-(p-chloro-alpha-phenylbenzyl)-4-(m-methylbenzyl)-piperazindihydrochlorid
1-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]-piperazindihyd
1-p-chlorbenzhydryl-m-methylbenzylpiperazinedihydrochloride
ancolandihydrochloride
bonamine
diadril
meclozinedihydrochloride
parachloraminedihydrochloride
Meclozine dihydrochloride monohydrate
Meclizine diHCl
1-(p-Chloro-a-phenylbenzyl)-4-(m-methylbenzyl)piperazine dihydrochloride
mecilizine hydrochloride
Navidoxine
NSC 28728
Piperazine, 1-(p-chloro-a-phenylbenzyl)-4-(m-methylbenzyl)-, dihydrochloride (6CI, 8CI)
Piperazine, 1-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]-, dihydrochloride (9CI)
Postafene dihydrochloride | [EINECS(EC#)]
214-164-8 | [Molecular Formula]
C25H29Cl3N2 | [MDL Number]
MFCD00058199 | [Molecular Weight]
463.87 | [MOL File]
1104-22-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White or yellowish-white, slightly hygroscopic, crystalline powder. | [Melting point ]
210.0 to 214.0 °C | [storage temp. ]
2-8°C
| [solubility ]
DMSO: soluble5mg/mL, clear (warmed) | [form ]
powder | [color ]
white to beige | [InChI]
1S/C25H27ClN2.2ClH/c1-20-6-5-7-21(18-20)19-27-14-16-28(17-15-27)25(22-8-3-2-4-9-22)23-10-12-24(26)13-11-23;;/h2-13,18,25H,14-17,19H2,1H3;2*1H | [InChIKey]
VCTHNOIYJIXQLV-UHFFFAOYSA-N | [SMILES]
[Cl-].[Cl-].Clc1ccc(cc1)C(N3CCN(CC3)Cc4cc(ccc4)C)c2ccccc2.[H+].[H+] | [CAS DataBase Reference]
1104-22-9(CAS DataBase Reference) | [EPA Substance Registry System]
1104-22-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R63:Possible risk of harm to the unborn child. | [Safety Statements ]
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
TL2005000
| [TSCA ]
TSCA listed | [HS Code ]
2933.59.8000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Repr. 2 | [Safety Profile]
Moderately toxic by
ingestion and intraperitoneal routes. An
experimental teratogen. Experimental
reproductive effects. When heated to
decomposition it emits very toxic fumes of
Cland NOx. | [Toxicity]
LD50 oral in mouse: 1600mg/kg |
| Hazard Information | Back Directory | [Description]
Meclizine is a histamine H1 receptor antagonist (Ki = 250 nM).1 Pretreatment with meclizine (2.5-30 mg/kg, i.p.) reduces ovalbumin-induced mast cell degranulation, edema, and leukocyte influx in rat lung.2 Formulations containing meclizine have been used in the treatment of motion sickness and vertigo. | [Chemical Properties]
White or yellowish-white, slightly hygroscopic, crystalline powder. | [Originator]
Antivert,Roerig,US,1957 | [Uses]
Antiemetic;Histamine antagonist | [Uses]
cholinergic, diagnostic aid | [Uses]
Meclizine Dihydrochloride is a histamine H1 receptor antagonist with antiemetic properties. Meclizine Dihydrochloride is a research product for neuroscience. This compound may exhibit neuroprotective properties. | [Manufacturing Process]
32.3 g of 1-p-chlorobenzhydryl-4-benzyl-piperazine, dissolved in 300 cm3 of alcohol are heated in an autoclave vessel, in the presence of Raney nickel, under a pressure of 100 kg H2, at about 150°C for 6 hours. The catalyst is filtered, the solvent is evaporated and the residue is fractionated under a high vacuum. p-Chlorobenzylhydryl-piperazine (BP 180° to 185°C/1 mm Hg) is isolated with a yield of 75%. Then finely ground NaNH2 is added. The mixture is heated under reflux for 1 hour, the mass is cooled and a molar equivalent of m-methyl benzyl chloride is added.
The solvent is evaporated and the residue is dissolved in chloroform. This
solution is washed with a saturated solution of K2CO3 and dried on K2CO3. The
solvent is evaporated and the residue is distilled under high vacuum. The
product of the condensation distills near 230°C at 2 mm Hg pressure and the
corresponding dihydrochloride melts at 217° to 224°C. | [Brand name]
Antivert (Pfizer). | [Therapeutic Function]
Antinauseant | [Biochem/physiol Actions]
Meclizine has the ability to increase glycolysis and decrease cellular ATP levels in media that has glucose and galactose. It guards the kidney against ischemia-reperfusion injury. Meclizine is considered as an anti-nausea and anti-dizziness drug, was identified in a ′nutrient-sensitized′ chemical screen. In human, it acts as an agonist of pregnane X receptor (PXR). It enhances the expression of CYP3A4 (cytochrome P450 3A4) mRNA and reduces CYP3A-catalyzed testosterone 6β-hydroxylation in primary cultures of human hepatocytes. | [Solubility in organics]
Meclizine dihydrochloride is readily soluble in chloroform and pyridine, slightly soluble in dilute acids and ethanol, and insoluble in water or ether.
| [storage]
Desiccate at RT |
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